Polymers from stabilized imines

Abstract

The disclosure describes new compositions and methods related to polyaminals and related polymers. The compositions are useful as therapeutic/drug conjugates, self-healing materials, reversible crosslinking materials, degradable hydrogels, protective coatings, and as metal scavenging agents. New atom efficient synthetic schemes are disclosed, which yield previously unobtainable high molecular weight polyaminals.

What is claimed is: 
     
       1. A polymer having the general structure 
       
         
           
           
               
               
           
         
         wherein R′ is an organic group, a hetero-organic group, or a hetero-atom; each X is an organic group, a hetero-organic group, a hetero-atom, or a hydrogen atom; and wherein at least two X groups are each a polyaminal segment —NH—CH 2 -Nuc-R″-Nuc-CH 2 —; and 
         wherein Nuc is a nucleophilic atom; and wherein R″ is an organic group or a hetero-organic group. 
       
     
     
       2. The polymer of  claim 1 , wherein R′ comprises at least one electron withdrawing or accepting group. 
     
     
       3. The polymer of  claim 2 , wherein the at least one electron withdrawing or accepting group is selected from the group consisting of: electronegative heteroatoms, positively charged groups, quaternary amine groups, conjugated groups, aromatic groups, halogens, nitriles, carbonyls, nitro groups, nitroso groups, sulfones, and sulfonates. 
     
     
       4. The polymer of  claim 1 , wherein R′ is a polymer group comprising at least 3 repeat units. 
     
     
       5. The polymer of  claim 1 , wherein at least one X group comprises at least one electron withdrawing or accepting group. 
     
     
       6. The polymer of  claim 5 , wherein the electron withdrawing or accepting group is selected from the group consisting of: electronegative heteroatoms, positively charged groups, quaternary amine groups, conjugated groups, aromatic groups, halogens, nitriles, carbonyls, nitro groups, nitroso groups, sulfones, and sulfonates. 
     
     
       7. The polymer of  claim 1 , wherein Nuc is an atom selected from the group consisting of: Si, Ge, Sn, N, P, As, Sb, O, S, Se, and Te. 
     
     
       8. The polymer of  claim 1 , wherein Nuc is a carbon atom. 
     
     
       9. The polymer of  claim 1 , wherein R″ is a polymer group comprising at least 3 repeat units. 
     
     
       10. The polymer of  claim 1 , wherein the polymer has an average molecular weight of at least 5,000 grams/mole. 
     
     
       11. A polymer having the general structure 
       
         
           
           
               
               
           
         
         wherein R′ is an organic group, a hetero-organic group, or a hetero-atom; each X is an organic group, a hetero-organic group, or a hetero-atom, a hydrogen atom; at least two X groups are each a polyaminal segment —NH—CH 2 —S—R″—S—CH 2 —; at least one X group comprises at least one electron withdrawing or accepting group; and R″ is an organic group or a hetero-organic group. 
       
     
     
       12. The polymer of  claim 11 , wherein R′ comprises at least one electron withdrawing or accepting group. 
     
     
       13. The polymer of  claim 12 , wherein the at least one electron withdrawing or accepting group is selected from the group consisting of: electronegative heteroatoms, positively charged groups, quaternary amine groups, conjugated groups, aromatic groups, halogens, nitriles, carbonyls, nitro groups, nitroso groups, sulfones, and sulfonates. 
     
     
       14. The polymer of  claim 11 , wherein R′ is a polymer group comprising at least 3 repeat units. 
     
     
       15. The polymer of  claim 11 , wherein R″ is a polymer group comprising at least 3 repeat units. 
     
     
       16. A polymer having the general structure 
       
         
           
           
               
               
           
         
         wherein R′ is an organic group, a hetero-organic group, or a hetero-atom; each X is an organic group, a hetero-organic group, or a hetero-atom, a hydrogen atom; at least two X groups are each a polyaminal segment —NH—CH 2 —S—R″—S—CH 2 —; at least one X group comprises at least one electron withdrawing or accepting group; and R″ is an organic group or a hetero-organic group, the polymer having an average molecular weight of at least 5,000 grams/mole. 
       
     
     
       17. The polymer of  claim 16 , wherein R′ comprises at least one electron withdrawing or accepting group. 
     
     
       18. The polymer of  claim 17 , wherein the at least one electron withdrawing or accepting group is selected from the group consisting of: electronegative heteroatoms, positively charged groups, quaternary amine groups, conjugated groups, aromatic groups, halogens, nitriles, carbonyls, nitro groups, nitroso groups, sulfones, and sulfonates. 
     
     
       19. The polymer of  claim 16 , wherein R′ is a polymer group comprising at least 3 repeat units. 
     
     
       20. The polymer of  claim 16 , wherein R″ is a polymer group comprising at least 3 repeat units.